Life Lessons

Being an entrepreneur is a huge financial sacrifice. You may not draw any salary while you’re bootstrapping and/or looking and begging for capital and even once you have the means to pay yourself, it will probably just barely be enough to keep the lights on. But that’s not the biggest cost of being an entrepreneur. Continue reading →

Many moons ago I spent the summer working in Porto, Portugal. At the time, the country was far less developed than the rest of Western Europe. Portugal was lightyears behind the economies and hustle and bustle of its neighbors. But the people were friendly, the weather was nice and the pace was slow and leisurely. One day while I was eating lunch by myself at a popular restaurant, the waiter asked if I would mind if another guest joined me since there were no empty tables. I assumed that was the local custom and acquiesced. After the initial awkwardness of breaking bread with a complete stranger subsided, we introduced ourselves and shook hands. I then followed with the obvious next question when getting to know someone: “So what do you do?” Continue reading →

I once left a perfectly good paying job with loads of student debt and almost no savings to my name to launch a company. I’ve flown planes, jumped out of planes, paraglided off 5,000 foot cliffs, scuba dived at night in shark infested waters and climbed mountains with gale force winds in sub-zero temperatures. But all of those activities pale in comparison to what has been far and away the most frightening thing I have ever done in my life. And that frightening thing was… Continue reading →

I was sitting on the floor in the back of an old single engine propeller-powered plane which was flying straight up toward the sky like a rocket ship. I was just a few feet away from the back door which was left open the entire ride. There were no seatbelts so I was not attached to the plane in any way nor was I attached to a parachute. One tiny hiccup of turbulence and that’s where my life’s story would have ended. I should mention that I was afraid of heights. Scratch that. I was terrified of heights. Needless to say, just 3 minutes into our climb my clothes were already drenched with sweat. In case you’re wondering, I did indeed inquire as to why the back door was left ajar, given our vulnerable seating arrangement in the aircraft. The matter-of-fact response I received was that it was a slight inconvenience to open it midflight. An “inconvenience”? I’d call my being spit out the back of a plane and falling at terminal velocity toward the earth a slightly bigger inconvenience. But I could tell nobody was particularly interested in hearing what I had to say on this matter so I just kept my opinion to myself, closed my eyes and prayed. [It’s uncanny how quickly atheists can become God-fearing in the face of imminent death.] Continue reading →

The receptionist escorted me to the conference room and said Mr. Stevens would be with me shortly. Mr. Stevens was the Chief Strategy Officer of a fast growing, Fortune 1,000 technology company. I was there to sell an expensive subscription to a suite of best practices research. I grabbed a seat and waited. And waited. Five minutes. Ten minutes. A half hour passed. I was about to get up and exit the scene when the door opened and in walked Mr. Stevens. He did not look happy. He didn’t shake my hand or even make eye contact. He walked to the opposite end of the room and took a seat, folded his arms and began his rant. “What the f*ck do you want? That woman who works for you asked me if I’d meet with you and I politely declined. I said I was busy and didn’t really have any need for your services. Then she called again the following week and the week after that and the week after. She wouldn’t stop. My admin said she called over fifty times over the course of the last six months. She refused to take no for an answer. She has been the biggest pain in the *ss of anyone I can think of since I began working here a decade ago. I now hate her, I hate your company and even though we just met, I hate you as well. I have zero and I mean literally zero interest in hearing anything you have to say but taking a meeting with you seemed to be the only way to get her to stop harassing me. So fine. Here I am. You got me. You win. Congratulations. So what the hell is so damn important that you just had to meet with me? And make it quick. You’ve got five minutes. I’m busy and I’ve got a thousand more important things to do with my time.” Continue reading →

I’ll never forget a deep sea fishing adventure I had over twenty years ago. It all started at business school during orientation week when I befriended a classmate from Florida over a couple beers. Jon and I became pretty good friends over those two years and would often get together to shoot the breeze about school, about careers, about life. It became quickly apparent that one of his passions was deep sea fishing. Correct that. His ONLY passion seemed to be deep sea fishing. He would somehow find a way to work the topic into just about any conversation. I couldn’t really relate but to each their own. Well, he was very interested in sharing his passion with me. Apparently, I had no idea what I was missing. So he invited me to crash at his house in Ft Lauderdale over the winter break and to experience this magnificent sport of deep sea fishing (to this day I still cringe when I use the words “fishing” and “sport” in the same sentence). I politely declined. I explained that I had already committed to the infinitely more riveting sport of watching paint dry. I thought that would be the end of that. I thought wrong. Not wanting to take no for an answer, I got the same invite over spring break that year and again over the following year’s winter and spring breaks. No, no and no. Finally, as we headed into our final week of school, Jon asked me one last time. At this point he was practically begging. I was starting to feel pretty guilty for repeatedly blowing him off those last couple years and I had exhausted my go-to list of excuses so this time I reluctantly accepted his invitation. And off to sunny Florida we went. Continue reading →

In the beautiful Boston suburb of Winchester, Senator Jason Lewis was giving a fiery presentation to a roomful of concerned parents, teachers and citizens. The topic was educational finance reform. Funding for education had been dramatically cut back in Massachusetts (and across the country for that matter) and something had to be done to stop the bleeding. Having intensely studied the challenges around the educational funding gap for years, he was well equipped to speak to this topic. He was resolute in his delivery. “I am committed to making sure that our cities and towns receive adequate and equitable resources in order to provide a second-to-none public education for our young people,” Senator Lewis assured the crowd. “And now I want you to feel empowered to have an impact on this critically important issue.” You could sense from the tone of his voice that this wasn’t just empty rhetoric. He cared deeply about the public school system and was committed to fixing the problem. As he methodically dissected the issues one at a time and recommended solutions to each of them, he could see the heads nodding in agreement. This was not an easy crowd to please but he had clearly done his homework. From the positive energy he was feeling from this discerning crowd, he knew in his gut that all the hard work was going to pay off. He was finally in a position to make a real difference. Continue reading →

I was returning to the San Carlos airport during my first ever solo flight. Everything went according to plan and I was now within sight of my destination. As I was preparing to go through the landing sequence like I had been taught during my many training flights, I called in to check on the wind speed. [Aircraft are designed to tolerate a certain amount of crosswind, beyond which the aircraft can easily flip over.] As a student pilot, my plane was designed for 10 knots of crosswind. 99% of the time, this wasn’t an issue for landing at this airport. But as luck would have it on this breezy day, I somehow managed to find myself in that 1% scenario. My crosswind speed at that moment was 13 knots. I was not off to an auspicious start. Continue reading →